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Author: Subject: Double bonds, amalgams and alklis
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[*] posted on 2-1-2018 at 05:31
Double bonds, amalgams and alklis

While researching some routes of synthesis of malonic acid grom glycerol, I ran at some interesting reactions:

1. Acrolein and HCl - anti-Markovnikov addition?

So, I'm referencing an the reaction at the bottom of page. Looks like that anti-Markovnikov addition is due to acrolein being Michael acceptor.

2. Acrylic acid and alkali

In segment 3. Discussion, they mentioned that b-hydroxypropionic acid can be synthesised from acrylic acid and strong alkali.
I guess that it's some kind od anti-Markovnikov addition of NaOH, for example, and Michael acceptor, acrylic acid.

Is that true or this is some completely different reaction?

3. Methacrylic acid

They mentioned 2 reactions that caught my eye - reducing double bond to single bond using amalgam, and complete removal of double bonded carbon by fusing acid and alkali.

So, this reactions gave me some ideas:

1. Allyl alcohol -> 1,3 propanediol

If reacting acrylic acid and alkali yields b-hydroxypropionic acid, maybe allyl alcohol would yield 1,3 propanediol.
Unless Michael acceptor is necessary for that reaction to work.

What are reaction conditions for such an reaction to occur?
I guess it doesn't involve high temperatures or anhydrous conditions, because in such conditions, b-hydroxypropionic acid would just decompose back to acrylic acid.

2. Allyl alcohol -> 1-propanol.

This is another use of allyl alcohol I got in mind. Is sodium amalgam reduction of double bonds "universal" or specific to some compounds, like methacrylic acid?

3. Destroying double bond by fusing with alkalis

This is more of general question - is there a name for reactions like that (methacrylic acid -> propanoic acid)?

Any help is welcome :)
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